Dean Winchester Does NOT Do Makeup
by feathers-theangel
Summary: The boys and their angels have followed a siren to it's newest hunting grounds - a gay bar. And the night they choose to kill it just so happens to be the night of a drag queen fashion show. Dean, Cas, and Gabriel get roped into going - and who can blame Dean for feeling fabulous? Pure Crack. Cas likes puns.


Dean Winchester did NOT do makeup. Nope.

"Oh, c'mon Dean. My ankle is sprained, I can't walk in heels." Sam said, pointing to his ace-bandage wrapped foot and the ice next to it.

"I told you- there is NO way in hell I am dressing up in drag. You couldn't make me do it for the world." Dean crossed his arms and leaned against the motel table, where Sam's laptop was open to a page advertising a drag-queen fashion show at a gay bar that had become the recent hunting grounds of a siren.

"Dean, more people are gonna die if you don't go tonight. He's already gone through six people!" Sam protested.

Gabriel looked up from the magazine he was flipping through on the other bed.

"He's right y'know. The siren could probably take out around four more, and those four could kill around one or two, and then it'll move on to the next town. You gotta start thinking with your brain here, Dean-o."

"You just wanna see me in drag." Dean growled.

"That's true." Gabriel responded, flicking through a couple pages. He sighed and looked up. "Look. I'm pretty sure it's not gonna go hunt in some stripper place in the next town. The last four towns he's targeted gay bars. He likes it there. And I'm pretty sure he's not gonna change that for you, my special little flower. Besides, with your face, you'll be the perfect target."

Sam smirked.

"Okay. Okay, fine. But you and Cas are coming with me." Dean rubbed the bridge of his nose.

"Deal." Gabe said, a grin lighting up his face. He snapped out, only to return with Cas and dresses and heels and makeup and wigs for the three of them. Sam burst out laughing when Cas asked why he was being forced to put on women's clothes when his vessel was a male and isn't it customary to frown upon things like this and Gabriel that's way too tight.

"Gabriel please, -" Cas' voice raised a few octaves. "No, really, Just get me something looser - no, Gabriel why are you stuffing tiny pillows into my dress-"

"Relax, baby bro. This'll make all the men look your way." Gabriel winked at him and smacked his ass, eliciting a yelp from Castiel. "Just put on the wig, I'll do your make up later."

Gabe started making his way towards Dean, who in turn started backing up.

"C'mon Dean-o, Cas is all dressed up already!"

"I- uh- I don't know-" Dean's back hit the table, and his hand hit a spoon, which launched the now-lukewarm pudding that Gabriel had been eating earlier straight into his face.

The room was dead silent until Cas decided to speak.

"I'm sorry Gabriel, but your misfortune is pudding a smile on my face." he deadpanned.

Gabriel stood there fuming as the brothers cracked up, and Dean looked up with tears streaming down his face to see Castiel standing next to the bed, the corners of his mouth curling up triumphantly.

"God, Cas. Where- where the hell did you pull that from?" Dean gasped, clutching his stomach.

"Well, it obviously wasn't his ass, because that's squeezed up nice and tight." Gabe commented, removing the pudding and grabbing Dean's arm at the same time. Gabriel popped them into a dressing room, with racks of clothing that covered two thirds of the walls and pushed Dean into a seat in front of a vanity table covered in makeup. A woman wearing a white jumpsuit popped into the room, took one look at Dean, and said, "You can't keep picking them up from the streets, Gabriel. Even if they're as pretty as this one. This is the last random makeover I'm doing. The last guy ruined my suit." She whined, pointing to her spotless white jumpsuit and pouting.

"Relax, Ariel, this one isn't a stray. It's Dean Winchester." The bastard pulled a lollipop out of nowhere and began sucking on it. "He needs a new wardrobe for a drag fashion show."

Ariel took another look at Dean and blinked. "Oh. Oh-Dean Winchester. Okay." She turned back to Gabriel. "But I still refuse to dress any more homeless men up like ducks or cover them with feather boas anymore, Gabriel."

Gabe pouted and stuck out his tongue at her, then poofed out.

"Okay, drag, drag, drag. Drag … " She ran her hands along the racks until she found the one she wanted, and pulled it back to him. On it, was several flapper dresses and things covered with feathers and sequins, metallic colored pants and a hell of a lot of feather boas. She looked at the rack and then looked back at him. "Okay- you stay here, I'm going to get your wig. Feel free to try anything on." She pressed a button on the vanity table, and suddenly music started blasting. Dean looked around for speakers, but his eyes landed on the rack of clothing next to him, and he got up to just - just look at his options. Yeah. See if there was anything loose.

He sifted through the clothing, pulling out several flapper dresses and one with a skirt made of neon yellow feathers. Along with this pile was a black and white feather boa, a pair of metallic tights, some boots, and a black plastic jacket. And no he definitely did NOT put on a ball gown and dance around with it. Well, maybe he did. But no one had to know that.

Ariel came back with a beach blonde chest length wig, which she carefully fastened to his head. She looked through his clothing choices and Dean held his breath, waiting for a quirked eyebrow or a judgmental stare, but all he got was a pile of clothing she picked out of the even bigger pile he had thrown on the floor.

"Get dressed." She told him, hands on her hips.

He stood there.

"What?" She questioned. Then she got it, and sighed. "Don't be such a little bitch. You're probably gonna have to tuck in your dick too, with those pants."

He flushed a deep red and stammered out something about how he already knew how and that he would really appreciate it if she left, which she did with an eye roll and a "hurry up".

Dean shed his clothing and shimmied into the pants with some difficulty, and managed to pull on the dress and jacket and boots with a little less trouble. It was severely uncomfortable, but hey, at least he looked good. He tossed one end of the neon pink boa over his shoulder and posed. Ariel had done his makeup after selecting his clothes, and it actually made it convincing. So who could blame him if he started dancing?

And that was when Gabriel decided to show up. Well, Dean didn't see him pop up, but he heard the distinct sound of someone inhaling sharply and then that same someone choking and coughing.

He spun around and saw Gabriel wearing a sparkly gold mini dress hunched over, purple in the face. He took a shuddering breath and suddenly barked out a sharp laugh, teetering in his heels and then falling into one of the racks. Dean started turning red at Gabriel's laughter.

After a few minutes Gabe had regained enough of himself to splutter "You … Were you - twerking?" This sent him into another round of hysterics. His laughing caused Ariel to poof in to see what the ruckus was, and then spent the next five minutes fixing Gabriel's wig and make up.

When they were ready, Gabriel took them back to the motel room, where Sam had the misfortune of being in the middle of sipping a milk shake. It was promptly spat out all over the bed.

"Dean?!" He choked. Dean turned red. Again.

"Can we just get this over with already?" Dean asked.

"It's okay, Dean, he's just surprised that you're a _spitting_ image of a woman." Cas commented.

Sam choked on his milkshake. Again.

Dean Winchester hates his life.

_  
Note: I'm not sure if I want to finish this, and if I do it's obviously going to lead to destiel, with it being a siren and all. Eh. Tell me what you think. I'm labeling this as Dean & Cas cause I'm pretty sure Im gonna at least post a second chapter with some 'Dean discovers new kink' sorta thing, but idk if i'm gonna follow them through all the events of the siren and drag show and whatnot. Anyways, enjoy!


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